CN113004200A - Formaldehyde concentration and pH value dual-response type probe based on naphthalimide derivative, and preparation and application thereof - Google Patents
Formaldehyde concentration and pH value dual-response type probe based on naphthalimide derivative, and preparation and application thereof Download PDFInfo
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Abstract
The application discloses a naphthalimide derivative-based formaldehyde concentration and pH value dual-response probe, which has a structural formula shown in formula (I):
Description
Technical Field
The invention relates to the field of active small molecules and pH detection application, in particular to a formaldehyde and pH dual-response probe based on a naphthalimide derivative, and preparation and application thereof.
Background
As a typical D-pi-A fluorescent dye, the naphthalimide derivative has the advantages of good conjugated system, better light stability, large Stokes shift/anti-Stokes shift and the like. In addition, the naphthalimide derivative is economical and easy to obtain, can modify a plurality of sites, and is easy to design and prepare various probes with excellent performance. In particular, probes using a naphthalimide derivative as a signal group have been widely used for visualizing enzymes, activated carbon clusters, activated oxygen clusters, activated nitrogen clusters, biological thiols, ions, internal environmental parameters, and the like in the fields of environment, food, life sciences, and the like. However, most probes based on naphthalimide derivatives are only capable of specifically recognizing a single analyte, and are not in line with the prevailing academic points of improving the "atom economy" and high density integration of compounds. Therefore, the development of the probe with double response type performance by taking the naphthalimide derivative as the probe parent nucleus has important scientific value and application value for expanding the application of the naphthalimide in the field of analysis and detection.
Formaldehyde, the smallest member of an activated carbon cluster, has many sources indoors or outdoors. A plurality of diseases can be caused by long-term exposure to the environment with high concentration of formaldehyde. Excessive formaldehyde concentrations are found in many necrotic or apoptotic cells and tissues, which in turn can trigger various pathological features such as leukemia, neurodegenerative diseases, alzheimer's disease, chronic liver and heart diseases.
pH is one of the important parameters of ecological balance. On a macroscopic level, the pH of samples such as domestic water, soil, rivers, etc. also affects the growth state of animals and plants. In 2006, the sanitary Standard for Drinking Water (GB5749-2006) issued by China stipulates that the pH value of drinking water should be between 6.5 and 8.5, and the dietary health of human bodies is guaranteed. The pH in the soil directly affects the metabolic activity of the cells of the plant roots and thus the osmotic pressure of the plant roots, which may lead to water loss in the plant, and the pH range which is best suited for plant growth has been documented and is generally between 5 and 8. In addition, the pH in the soil or river may also affect the type and quantity of microorganisms therein.
In conclusion, the method has very important practical significance for detecting the concentration and the pH value of the formaldehyde in the environment.
Disclosure of Invention
The application provides a naphthalimide derivative-based formaldehyde concentration and pH value dual-response type probe and preparation and application thereof.
The first purpose of the application is to provide a formaldehyde concentration and pH value dual-response type probe based on naphthalimide derivatives, wherein the structural formula of the formaldehyde concentration and pH value dual-response type probe is shown as a formula (I):
the second object of the present application is to provide a method for preparing the formaldehyde concentration and pH dual-responsive probe, comprising:
sequentially adding a compound shown as a formula (II), a solvent, a compound shown as a formula (III), acetic acid and a reducing agent into a reactor at 0 ℃, and then placing the reactor at 20-30 ℃ for reaction; after the reaction is finished, separating and purifying the reaction liquid to obtain the dual-response probe shown in the formula (I);
the reaction formula is as follows:
optionally, the amount ratio of the compound shown in the formula (II), the compound shown in the formula (III) and the reducing agent to the acetic acid is 1: 1-1.5: 4: 10; the solvent is tetrahydrofuran; the reducing agent is sodium triacetoxyborohydride; the reaction time is 8-12 h.
Optionally, the separation and purification is as follows: and (3) carrying out reduced pressure rotary evaporation on the reaction liquid to remove the solvent, taking the concentrate for column chromatography separation, taking dichloromethane-methanol mixed liquor with the volume ratio of 40:1 as a developing agent, and eluting the target product to obtain the dual-response type probe shown in the formula (I).
The compounds of formula (II) used in the present invention are disclosed, and the preparation method thereof can be referred to in the literature (Xie Z, Ge J, Zhang H, et al. A high selective two-photon fluorogenic probe for reactive and biochemical applications in cells and zebrafish [ J ]. Sens. activators B,2017,241,1050-1056).
The compound represented by the formula (III) used in the present invention is a compound disclosed, and the preparation method thereof can be referred to in the literature (Liu C, Zhang R, Zhang W, et al, "Dual-Key-and-Lock" ruthenium complex probe for lysosomal for molecular sieves cells and regulators [ J ]. J.Am.chem.Soc.,2019,141,8462-8472).
The third purpose of the present application is to provide the application of the dual-response probe in formaldehyde concentration and pH detection, specifically:
the application provides an application of the formaldehyde concentration and pH value dual-response type probe in preparation of a reagent for detecting formaldehyde concentration.
The application provides an application of the formaldehyde concentration and pH value dual-response type probe in preparation of a reagent for detecting a pH value.
The application provides an application of the formaldehyde concentration and pH value dual-response type probe in preparation of a reagent capable of detecting both formaldehyde concentration and pH value.
The application also provides a method for quantitatively detecting the concentration or the pH value of formaldehyde, which is used for the detection of environmental samples and other non-diagnosis and treatment purposes and comprises the following steps:
(1) adding the formaldehyde concentration and pH value dual-response type probe into a solution to be detected, and uniformly mixing;
(2) collecting the fluorescence intensity of the solution to be detected under the conditions that the excitation wavelength is 440nm and the emission wavelength is 555nm, and calculating according to a standard curve to obtain the formaldehyde concentration of the solution to be detected; and/or: and collecting the absorbance of the solution to be detected under the absorption wavelength of 460nm, and calculating according to the standard curve to obtain the pH value of the solution to be detected.
The double-response probe provided by the invention can be used for quantitatively detecting formaldehyde in a solution, and the detection method comprises the following steps:
and adding the dual-response probe into the solution to be detected, uniformly mixing, collecting the fluorescence intensity of the solution to be detected under the conditions that the excitation wavelength is 440nm and the emission wavelength is 555nm, and calculating according to a standard curve to obtain the formaldehyde concentration of the solution to be detected.
Optionally, the final concentration of the dual-response probe added to the solution to be detected is 0.01mM, and the final concentration and the formaldehyde concentration value of the solution to be detected are in a good linear relation when being 0-4 mM, so that quantitative detection of the formaldehyde concentration of the solution to be detected within the concentration range can be realized.
Alternatively, the standard curve is prepared as follows:
and (3) respectively reacting the 0.01mM fluorescent probe with a solution with formaldehyde concentration of 0-4 mM, collecting the fluorescence intensity of the solution to be detected under the excitation wavelength of 440nm and the emission wavelength of 555nm, and drawing by taking the fluorescence intensity as a vertical coordinate and the formaldehyde concentration of the solution to be detected as a horizontal coordinate to obtain a linear standard curve.
The double-response probe provided by the invention can be used for quantitatively detecting the pH value in a solution, and the detection method comprises the following steps:
and adding the dual-response probe into the solution to be detected, uniformly mixing, collecting the absorbance of the solution to be detected under the absorption wavelength of 460nm, and calculating according to a standard curve to obtain the pH value of the solution to be detected.
Optionally, the final concentration of the dual-response probe added to the solution to be detected is 0.01mM, and the dual-response probe has a good linear relationship with the pH value of the solution to be detected being 7.25-8.5, so that the quantitative detection of the pH value of the solution to be detected within the pH value range can be realized.
Alternatively, the standard curve is prepared as follows:
and (3) respectively reacting the 0.01mM fluorescent probe with a solution with the pH value of 7.25-8.5, collecting the absorbance of the solution to be detected under the absorption wavelength of 485nm, and drawing by taking the absorbance as a vertical coordinate and the pH value of the solution to be detected as a horizontal coordinate to obtain a linear standard curve.
Compared with the prior art, the method has at least one of the following beneficial effects:
(1) the development of the probe with double/multi-response performance can expand the application of the naphthalimide derivative in the fields of environment, food, life science and the like, and is in line with the mainstream academic viewpoint of improving the atom economy and high-density integration of the compound.
(2) The implementation of the invention expands the application range of the naphthalimide derivative and has better scientific research value and practical application value in the detection field.
(3) The double-response probe provided by the application has the advantages of mature synthesis mechanism, simple preparation method and good selectivity, and can realize accurate quantitative detection of the concentration and the pH value of formaldehyde in a solution.
Drawings
FIG. 1 shows a nuclear magnetic hydrogen spectrum of the probe (I) prepared in example 1.
FIG. 2 is a high-resolution mass spectrum of the probe (I) prepared in example 1.
Fig. 3 is a fluorescence titration graph and a working curve graph (excitation wavelength 440nm, emission wavelength 555nm) of the probe (I) prepared in example 1 for formaldehyde recognition under the condition of DMSO/PBS buffer (pH 4.0, v/v 1/50).
FIG. 4 is a graph showing the interference resistance of the probe (I) prepared in example 1 to common bioactive molecules (1 to 7 are formaldehyde, methylglyoxal, acetaldehyde, homocysteine, cysteine, glucose and sodium pyruvate; excitation wavelength is 440nm, and emission wavelength is 555nm, respectively).
Fig. 5 is a graph of uv-vis spectra of the probe (I) prepared in example 1 added to DMSO/PBS buffer (v/v-1/50) at different pH, and a linear relationship of absorbance and pH (absorption wavelength 460 nm).
FIG. 6 is a histogram of the absorbance of probe (I) prepared in example 1 in DMSO/PBS buffer (pH 9, v/v 1/50) in the presence of different active molecules. (1-7 are formaldehyde, methylglyoxal, acetaldehyde, homocysteine, cysteine, glucose and sodium pyruvate respectively; absorption wavelength 460 nm).
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
The following is a description of specific examples:
example 1: preparation of Probe (I)
Sequentially adding a compound (II), anhydrous tetrahydrofuran, a compound (III), acetic acid and sodium triacetoxyborohydride into a 25mL round-bottom flask at the temperature of 0 ℃, wherein the mass ratio of the compound (II), the compound (III), the acetic acid and the sodium triacetoxyborohydride is 1:1.2:10:4, the compound (II) is 0.2mmol, and the amount of the anhydrous tetrahydrofuran is 5 mL. Followed by stirring at a reaction temperature of 25 ℃ for 10 h. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography eluting with dichloromethane/methanol 40:1, v/v to give 51mg of a yellow solid in 49.2% yield. The nuclear magnetic hydrogen spectrum is shown in figure 1, and the high-resolution mass spectrogram is shown in figure 2.
1H NMR(400MHz,CDCl3-d)δ8.75(d,J＝2.3Hz,1H),8.57(dd,J＝8.6,2.3Hz,1H),8.33–8.29(m,2H),8.09(d,J＝8.7Hz,1H),7.87(s,1H),7.55(t,J＝7.8Hz,1H),5.91–5.81(m,1H),5.30–5.24(m,2H),4.62(dd,J＝7.8,5.6Hz,1H),4.16–3.93(m,5H),2.83–2.65(m,2H),1.69–1.62(m,2H),1.45–1.39(m,2H),0.96(t,J＝7.3Hz,3H).HRMS(ESI)calcd.for C27H26N4O7[M]-517.1801,found517.1735.
Example 2: fluorescence spectroscopy of probe (I) (10. mu.M) response to formaldehyde.
An amount of the probe (I) (prepared in example 1) was accurately weighed, a probe stock solution having a concentration of 0.05mM was prepared from dimethyl sulfoxide, a pipette gun pipetted a predetermined amount of the probe solution, the probe solution was added to PBS buffer, formaldehyde was added to different concentrations, the final mixed solution was DMSO/PBS buffer (1:50, v: v, pH 4.0), the final concentration of the probe was 10. mu.M, and the final concentrations of formaldehyde were 0mM, 0.25mM, 0.5mM, 1mM, 2mM, 3mM, 4mM, 5mM, 6mM, 7mM, 8mM, 9mM, 10mM, 15mM, respectively, and the reaction was carried out at 37 ℃ for 3 hours, and the probe (I) was added to a 96-well plate and the change in the fluorescence spectrum of the probe (I) was measured with a multifunction microplate reader, and a graph was prepared. The excitation wavelength is 440nm, and the emission wavelength is 555 nm.
As shown in FIG. 3 (a), the fluorescence intensity of probe (I) increases as the concentration of formaldehyde increases. Therefore, the probe (I) can have the response capability to formaldehyde. As shown in FIG. 3 (b), the fluorescence intensity at 555nm of probe (I) was in a good linear relationship with the formaldehyde concentration (0 to 4mM) (linear regression equation: y: 53.15x +79.52, R)2＝0.99)。
Example 3: selective study of Probe (I) (10. mu.M) on Formaldehyde
Accurately weighing a certain amount of probe (I) (prepared in example 1), preparing a probe mother solution with the concentration of 0.05mM by using dimethyl sulfoxide, absorbing a certain amount of probe solution by using a pipette gun, adding the probe solution into a PBS buffer solution, then adding different active molecules (formaldehyde, methylglyoxal, acetaldehyde, homocysteine, cysteine, glucose and sodium pyruvate in sequence), enabling the final mixed liquid system to be the DMSO/PBS buffer solution (1:50, v: v, pH 4.0), enabling the final concentration of the probe to be 10 mu M, enabling the final concentrations of the formaldehyde, the glyoxal, the acetaldehyde, the glucose and the sodium pyruvate to be 5mM respectively, enabling the concentrations of the homocysteine and the homocysteine to be 1mM, reacting for 3h at 37 ℃, finally adding the probe (I) into a 96-well plate, measuring the change condition of the fluorescence spectrum of the probe (I) by using a multifunctional microplate reader, and making a fluorescence intensity histogram. The excitation wavelength is 440nm, and the emission wavelength is 555 nm.
As shown in FIG. 4, the fluorescence intensity of probe (I) at 555nm in the presence of other related bioactive molecules except formaldehyde is not substantially changed, which indicates that the anti-interference capability of the probe (I) is very good, i.e., the probe (I) has better fluorescence response selectivity to formaldehyde.
Example 4: UV-VIS Spectroscopy of the response of Probe (I) (10 μ M) to pH.
A certain amount of the probe (I) (prepared in example 1) was accurately weighed, a probe stock solution with a concentration of 0.05mM was prepared from dimethyl sulfoxide, 8. mu.L of the solution was pipetted into 390. mu.L of PBS buffer solution, DMSO/PBS buffer solutions (1:50, v: v, pH 4.0, 5.0, 5.5, 6.0, 6.5, 7.0, 7.25, 7.5, 8.25, 8.5, 9.0, 9.5, 11 in this order) were prepared such that the final concentration of the probe was 10. mu.M, the probe was shaken well and then added to a 96-well plate, the change in the UV-visible spectrum of the probe (I) was measured using a multifunctional microplate reader, and a relevant linear curve was prepared.
As shown in FIG. 5 (a), the probe (I) showed an increasing absorbance with decreasing pH, and the fluorescence intensity at 460nm was well linearly dependent on pH in the range of 7.25 to 8.5 (linear regression equation: Abs 0.08 ═ pH [. sup.]－0.519,R20.99) (fig. 5 (b)). The pKa of the probe was found to be 7.81 as calculated by the Henderson-Hasselbalch equation (FIG. 5 (c)).
Example 5: selective study of Probe (I) (10. mu.M) on pH
A certain amount of the probe (I) (prepared in example 1) was accurately weighed, a probe mother solution with a concentration of 0.05mM was prepared from dimethyl sulfoxide, 8. mu.L of the probe mother solution was pipetted by a pipette, and added to 390. mu.L of a probe mother solution containing bioactive molecules (formaldehyde, methylglyoxal, acetaldehyde, homocysteine, cysteine, glucose and sodium pyruvate in this order) so that the final mixed solution system was DMSO/PBS buffer (1:50, v: v, pH 4.0) and the final concentration of the probe was 10. mu.M, wherein the final concentrations of formaldehyde, methylglyoxal, acetaldehyde, glucose and sodium pyruvate were 5mM and the final concentrations of homocysteine and cysteine were 1mM, and the probe (I) was shaken and added to a 96-well plate to measure the change of the UV-visible spectrum of the probe (I) with a multifunctional microplate reader.
The fluorescence spectrum is shown in FIG. 6. The data show that several important bioactive molecules have little effect on the fluorescence signal of probe (I) in PBS buffer at pH 9.0. The experimental data show that the probe has good anti-interference capability.
The above-mentioned embodiments only express several embodiments of the present application, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the concept of the present application, which falls within the scope of protection of the present application. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (8)
1. A naphthalimide derivative-based formaldehyde concentration and pH value dual-response probe is characterized in that the structural formula of the formaldehyde concentration and pH value dual-response probe is shown as the formula (I):
2. the method for preparing the formaldehyde concentration and pH value dual-response type probe according to claim 1, comprising:
sequentially adding a compound shown as a formula (II), a solvent, a compound shown as a formula (III), acetic acid and a reducing agent into a reactor at 0 ℃, and then placing the reactor at 20-30 ℃ for reaction; after the reaction is finished, separating and purifying the reaction liquid to obtain the dual-response probe shown in the formula (I);
3. the preparation method according to claim 2, wherein the mass ratio of the compound represented by the formula (II), the compound represented by the formula (III), and the reducing agent to the acetic acid is 1:1 to 1.5:4: 10; the solvent is tetrahydrofuran; the reducing agent is sodium triacetoxyborohydride; the reaction time is 8-12 h.
4. The method of claim 2, wherein the separation and purification is: and (3) carrying out reduced pressure rotary evaporation on the reaction liquid to remove the solvent, taking the concentrate for column chromatography separation, taking dichloromethane-methanol mixed liquor with the volume ratio of 40:1 as a developing agent, and eluting the target product to obtain the dual-response type probe shown in the formula (I).
5. Use of the formaldehyde concentration and pH dual-response probe according to claim 1 for preparing a reagent for detecting formaldehyde concentration and/or pH.
6. A method for the quantitative determination of formaldehyde concentration or pH for non-diagnostic and therapeutic purposes, comprising:
(1) adding the formaldehyde concentration and pH value dual-response type probe into a solution to be detected, and uniformly mixing;
(2) collecting the fluorescence intensity of the solution to be detected under the conditions that the excitation wavelength is 440nm and the emission wavelength is 555nm, and calculating according to a standard curve to obtain the formaldehyde concentration of the solution to be detected;
or: and collecting the absorbance of the solution to be detected under the absorption wavelength of 460nm, and calculating according to the standard curve to obtain the pH value of the solution to be detected.
7. The quantitative determination method according to claim 6, wherein, in the case of detecting the formaldehyde concentration, the ratio of the final concentration of the formaldehyde concentration and the pH value dual-response type probe in the solution to be detected to the formaldehyde concentration is 0.01 mM: 0 to 4 mM.
8. The quantitative determination method according to claim 6, wherein the final concentration of the formaldehyde and pH dual-responsive probe added to the test solution is 0.01mM and the pH of the test solution is 7.25 to 8.5 when the pH is measured.
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Cited By (2)
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|---|---|---|---|---|
| CN114149369A (en) * | 2021-12-14 | 2022-03-08 | 河南省农业科学院农业质量标准与检测技术研究所 | Fluorescent probe FAL1 for formaldehyde and pH dual-function detection and preparation method and application thereof |
| CN114149369B (en) * | 2021-12-14 | 2024-02-06 | 河南省农业科学院农业质量标准与检测技术研究所 | Fluorescent probe FAL1 for formaldehyde and pH dual-function detection, and preparation method and application thereof |
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| CN113004200B (en) | 2022-02-18 |
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